N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide

Base Information

• Chemical Name: N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide
• CAS No.: 145122-93-6
• Molecular Formula: C₂₂H₃₀N₂O₄S
• Molecular Weight: 418.557
• Mol file: 145122-93-6.mol

Synonyms:N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide

Chemical Property of N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide

There total 6 articles about N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

acetic anhydride (108-24-7) + (2S,2'S,3'S)-N-(2'-amino-3'-phenylbutanoyl)bornane-10,2-sultam (145122-92-5) → N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide (145122-93-6)

Guidance literature:

With pyridine; for 6h; Ambient temperature;

DOI:10.1002/hlca.19920750622

Reference yield:

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7) → N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide (145122-93-6)

Guidance literature:

Multi-step reaction with 5 steps

2: 1) NaN(TMS)2 / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 30 min.

3: 79 percent / 1 N aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 79 percent / Zn-powder, 1 N aq. HCl, AcOH / 20 h / 25 °C

5: 99 percent / pyridine / 6 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hexamethyldisilazane; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1002/hlca.19920750622

Reference yield:

phenyllithium (591-51-5) → N-[(1S,2S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-phenyl-propyl]-acetamide (145122-93-6)

Guidance literature:

Multi-step reaction with 5 steps

2: 1) NaN(TMS)2 / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 30 min.

3: 79 percent / 1 N aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 79 percent / Zn-powder, 1 N aq. HCl, AcOH / 20 h / 25 °C

5: 99 percent / pyridine / 6 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hexamethyldisilazane; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1002/hlca.19920750622

upstream raw materials:

acetic anhydride

(2S,2'S,3'S)-N-(2'-amino-3'-phenylbutanoyl)bornane-10,2-sultam

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one

phenyllithium

Downstream raw materials:

(2S,3S)-N-acetyl-β-methylphenylalanine